Water → HCID 22117537, 화합물

HRID 1275795노트

반응식

HRID 1275795 반응식
[C-:1]#[CH:2].[Li+].C(N)CN.Br[C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.O>CN(P(N(C)C)(N(C)C)=O)C.CCOCC>[C:1]([C:9]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2)#[CH:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 2316249-Bromo-9-phenylfluoreneHCID 2724010Lithium acetylide-ethylenediamine (1:1)

생성물 1

HCID 22117537HCID 22117537, 화합물

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 12679Hexamethylphosphoramide용매2회

실험 절차

Lithium acetylenide-ethylenediamine (10 mmol) is added to a dry flask under argon, diluted with 5 mL of HMPA, and cooled to between 0 and 5° C. with stirring. A solution of 8 mmol of 9-bromo-9-phenylfluorene dissolved in 4 mL of HMPA is added slowly to the reaction flask. The reaction mixture is warmed to room temperature and, after 2 h, 25 mL of water is slowly added. The mixture is taken up in 100 mL of ether and washed with 20mL of H2O, 20 mL of brine, dried (Na2SO4) and concentrated. The product is purified by chromatography over SiO2 using EtOAc/hexanes (2/98) as eluent. (Smith, W. N.; Beumel, O. F., Preparation of Alkynes with Dialkynes by reaction of monohalo- and dihaloalkanes with lithium acetylenide-ethylenediamine complex., Synthesis, 1974, 441-442.)

후처리

  1. temperaturecooled to between 0 and 5° C.
  2. additionis added slowly to the reaction flask
  3. washwashed with 20mL of H2O, 20 mL of brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe product is purified by chromatography over SiO2
  7. custom, Preparation of Alkynes with Dialkynes
  8. custom, Synthesis, 1974, 441-442

출처 및 근거

ORD 기록
ord-4c246467f63049019e2974f0045eb015
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06162824

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